Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, Prosp Oktyabrya 141, 450075 Ufa, Russian Federation.
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, Prosp Oktyabrya 141, 450075 Ufa, Russian Federation.
Steroids. 2019 Aug;148:28-35. doi: 10.1016/j.steroids.2019.04.007. Epub 2019 May 7.
20R-Hydroxy short-chain ecdysteroids were synthesized by chemo- and stereoselective reduction of poststerone acetonide with L-Selectride or LiAlH. The same reaction with the excess of L- Selectride followed by the treatment of the reaction mixture with hydrochloric acid is accompanied by (8R)-13(14 → 8)abeo- rearrangements, which resulted in the contraction/expansion of C/D pregnane rings. The reaction of 20R-hydroxy poststerone analogs with (diethylamino)sulfur trifluoride (DAST) proceeds through intramolecular rearrangements and provides D-homo- or 13,14-seco- androstane structures.
20R-羟基短链蜕皮甾类通过后甾酮缩酮与 L-Selectride 或 LiAlH 的化学和立体选择性还原合成。用过量的 L-Selectride 进行相同的反应，然后用盐酸处理反应混合物，会伴随（8R）-13（14 → 8）abeo-重排，导致 C/D 孕烷环的收缩/扩张。20R-羟基后甾酮类似物与（二乙氨基）三氟化硫（DAST）的反应通过分子内重排进行，并提供 D-同型或 13,14-断和甾烷结构。
